Why You Need to Start Failing!

Or...Why Embracing Epic Fails is Your Secret to Success

My very first boyfriend was a car guy. Like drawing me a picture of a Porsche on love notes, missing his surprise birthday (organized by me, of course) because he was helping a friend’s Dad restore a Porsche, and worshipping his brand new Honda Accord like she was the goddess Venus kind of car guy. In that Honda Accord, we snuck away to the Swim Club parking lot for steamy make-out sessions and sped to parties where we swigged Yukon Jack from those adorably tiny bottles... and it was that Honda Accord I crashed into a mailbox and made my seventeen-year-old boyfriend cry.

It was his fault. I told him I didn’t want to learn how to drive and especially didn’t want to drive a stick shift. He convinced me it was easy, and he made it look easy. He was so sexy, easing his foot down on the clutch, shifting, and zooming off into the sunset (I always find competence sexy, and that was about the only thing a seventeen-year-old boy could be competent at). Now, you can probably tell by the fact he owned a brand new Honda Accord, that boyfriend lived in an “upscale” neighborhood of the eighties. The kids that lived in these neighborhoods wore ski jackets with their collection of lift tickets hanging off, Lacoste polo shirts, and Docksiders with no socks. They bought their girlfriends cashmere sweaters and Obsession perfume for their birthdays (true story, I had owned neither before).

On the fateful day of the mailbox catastrophe, we had barely left his driveway and were cautiously navigating through his pristine neighborhood. Boyfriend considered this the perfect place to teach me to drive. A non-seventeen-year-old would have taken a trembling sixteen-year-old to a parking lot. It started well. I actually got out of first gear, and as the Honda drifted toward the gentle curve of a cul-de-sac, I wasn’t thinking too much about steering as I was waiting to shift again. You know that moment when you’re so focused on not messing up, you forget the basics? When the boyfriend noticed me drifting toward the curb, he yelled, “Brake! Brake!” His voice, dripping with terror, sent me into a panic—my foot shot up and slammed down on... the accelerator.

His Mom hated me. I was most definitely from the wrong side of the tracks (or, in this case, Route 206), but the car repair bill and making her beloved baby cry cemented her opinion. Every time he encouraged her to pick me up when they saw me walking to school, her perfectly made-up face scrunched with resentment when she glared at me in the rearview mirror.

I didn’t drive again until I was twenty-two years old. Why? Because one tiny failure can make you believe you are completely and utterly hopeless at what you were trying to do. One tiny failure can convince your traitorous brain that you can’t do anything, that you will fail at everything, and that failure is the absolute worst thing that could happen to you.

But it’s not the end. You know what’s worse than failing? Standing still, going nowhere.

Are you feeling stagnant? Do your dreams seem so unattainable you only dare think of them at night when the lights are out and the hectic, stressful day is safely behind you? Are you ignoring those dreams? Or pushing them away? Perhaps, like I was, you’re stagnant because you are afraid to fail. If you go after your dreams, then everyone will laugh at you, you’ll lose all your money, you’ll get fired, and you’ll probably die in a drainage ditch where a stray dog will find you and gnaw at your juicy thighs.

Since the day I crushed my boyfriend’s neighbor's mailbox, I have faced failure and had flop after flop. But the fear of failing no longer hinders me. I have learned how to fail forward and can teach you too. After I’m done with you, you’ll be running into the world searching for projects you can screw up! (I am kidding here. Just kidding). When you fail forward, you move into a challenge with an understanding and acceptance of the possibility of failure. If the worst happens, you learn big, giant lessons from the experience and take big, giant steps away from your mistakes. Forward. Onward and upward. So maybe your car’s bumper gets knocked off by a neighbor’s badly placed mailbox (who decided to put them at the end of the driveway, anyway? I mean, they’re just asking to be crushed) – so you pick it up, toss it in the back seat, and head to the liquor store to sweet-talk some guy into buying you a bottle of Yukon Jack.

Don’t get me wrong, the first few failures are hard. In fact, they’re terrifying. But, fail, you must to get beyond the fear that not only will you be dead, but the dog will wander off because your thighs are, in fact, not that juicy. So, let’s team up today and tackle that first dreaded flop head-on with my fail-forward formula. If your efforts fail, great - you’ve learned that failing doesn’t kill you, and next time, you’ll take bigger risks, enjoy bigger rewards, and have the chance to get your art/business/opinions out into the world. If your efforts succeed? Well, look what launching with a plan for failure did for you. So here’s your “Let’s Get You To Experience Failure, So That You Know It Won’t Kill You, So You Realize The Benefits, So You Are No Longer Incapacitated so that The World Can Experience The True You” plan.

Step 1: Choose Your Journey.

Here’s the checklist for the perfect “fail forward” journey.

• The journey shouldn’t cost you any money

• The journey shouldn’t take more than a day

• You can see the results of the journey immediately

This list takes the procrastination technique, “Oh, I can’t afford to lose time and money,” off the table. That’s an issue you’ll face in later failures, but give yourself a break just now - you are only practicing a single bar; we don’t expect you to play the whole symphony. Part of this exercise is to know immediately if you have failed or succeeded. You can’t escape me by choosing something that won’t fail you forward until six months from now (a great diversionary tactic).

I’m going to use a fake journey as a running example. For the purposes of this article, let’s assume your journey is a decision to sell the paintings you’ve been hiding in the back of your closet behind your purple cowboy boots.

• Money - Your neighbour has agreed you can set up a table at her yard sale

• Time - Her yard sale is a single day

• Immediacy - You’ll either sell a painting or you won’t

Step 2: Find The Real Worst-Case Scenario.

The truth you probably don’t want to hear... you have no idea what you are afraid of. If you’re like I was, then you avoid possible failure with vague excuses like: “I will die,” “I will ruin my career,” or “The world will hate me.”

So before you start your journey, please do me a favor, bust out your journal and your glittery pen, and write down the worst-case scenario. In the example journey, maybe a famous art critic is fraternizing local garage sales, hunting for a vintage pink Lacoste polo shirt like her boyfriend used to wear in the eighties. The critic comes across your table replete with your creations and is so disgusted by them she sets the table alight, and all of your work burns to the ground. Once you’ve finished documenting your worst-case scenario, ask yourself, “Could that realistically happen?” (*Clears throat* Uh…no!) If it could NOT realistically happen. Try again. Write something that could happen, like you don’t sell a painting.

With your glittery pen ready, let’s dive into a vivid daydream session. Visualize every detail of this failure - what constituted failure? How did people react? How did it make you feel? Now, write that story down. This is the actual worst-case scenario. And you know what? It’s not that bad.

Using our example. Pre-Step 2: A famous art critic burns down your table, and you lose a lifetime of work. Question: Could that happen? Really? No. The worst-case scenario is that you won’t sell anything, and you’ve written the story of that failure. Post Step 2: No one wants your paintings, and it makes you feel crappy (feeling crappy is a far cry from losing your life’s work.)

Step 3: Quantify & Visualize Success

Your project may be a success, and yet you still view it as a failure. You avoid that mistake by quantifying what success looks like (and again, be realistic). When I was sixteen, my version of success probably looked like “driving around a parking lot in an automatic car without crashing.” It’s all I needed and would have moved me through my fear. But the version of success I gave myself was, “drive a brand new stick-shift Honda Accord really fast around a rich neighborhood and impress my boyfriend.” No wonder I failed.

Write your measure for success. Once you have quantified the minimum success, you are again free to daydream. Visualize a raging success. What happened? What did it look like? How do you feel? Write that story to dispel your worst-case scenario from your mind.

Using our example: Pre Step 3: This project won’t be successful unless I sell 25 paintings for my top price. Post Step 3: This would be a success if I had some friendly chats with people or if someone said something nice about a painting. Maybe I gave out a few cards.

Step 4: Document Your Fail Forward Theories

To learn from your failures, or fail forward, you must analyze and document why your project failed. Before your journey, list all the reasons you can come up with that this project might fail. Remember, you only have a day, so launch something “good enough.” It doesn’t have to be perfect.

Using our example: Pre Step 4: My paintings suck, and no one will buy them. Post step 4: Maybe my neighbor’s yard sale, comprising her old beanie-baby collection and her son’s old comic books, wasn’t the best place to try to sell sophisticated modern art.

Step 5: Launch

Set Up your table. Unpack your paintings. Smile. Just ship it. Take a deep breath.

Step 6: Succeed or Fail Forward

This is the fun part. Honestly! And when you look at your journey as pure fun or a playful experiment, it becomes easier to deal with disappointments or unexpected results. You know what success looks like. You have quantified it. Was your journey successful?

Notice I said, was your journey successful? Not were YOU successful?

If your project was unsuccessful, here is where the fun begins. It’s time to fail forward and gather as much data as possible so you can quickly jump back on your horse and ride again.

Test your theories. You can gather anecdotal and quantifiable evidence to help you do this. My favorite way is to ask the people involved. What were you hoping to buy? Would you ever imagine buying a painting like this? Do you buy paintings at all? What kind?

Don’t only examine why you failed. Get clear about your successes and the reasons behind them. When you finish testing your theories, you should have some superb data to help you fail forward. Using this data, you focus on the elements of success, learn from your failures, create new theories, and relaunch your journey.

Using our example: Pre Step 6: No one bought a painting! No one talked to me. Most people avoided my table! I must be such an unpleasant person. Post Step 6: No one bought a painting, but I had a couple of delightful conversations. One woman told me she had no room for paintings because she reserved her wall space for the shelves displaying her beanie baby collection. No one admired the paintings or showed interest, but the cheapest one had a visible price tag of $500. Maybe next time, I won’t sell at a garage sale, and I won’t include such visible prices to encourage conversation.

Step 7: Repeat

When you fail forward, you not only keep your momentum going but also put yourself on a constant cycle of improvement. It’s a simple formula: Prepare, Journey, Learn, Journey Again.

Failure is not the big bad wolf at your door; it’s the knock that lets you know opportunity has arrived, and it’s time to tell your boyfriend you think he’s so sexy driving that brand new Honda Accord, you’d rather stay right where you are in the passenger seat where you can watch him. You’ll learn to drive in your dad’s automatic station wagon in the Acme parking lot.

JOURNAL PROMPT:

Get going! Pick a journey and fail forward.

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